She was bullied at school, didn’t fit in at university, and spent the first 20 years of her life trying to make herself smaller. Today, Alex Depledge MBE is a serial tech entrepreneur who has built and sold multimillion-pound businesses, and was appointed the country’s first ever Entrepreneurship Advisor to the Chancellor.
In this episode, Anna sits down with Alex for a candid and compelling conversation about money, ambition, and what it really takes to back yourself when the world isn’t quite ready for you.
Alex talks openly about the emotional reality of entrepreneurship, what it actually costs, and why the moment she stopped trying to fit in was the moment everything changed. She shares why failure is so much more valuable than we give it credit for, and what she has learned from building and selling multimillion-pound businesses.
They also get into the bigger picture. What AI really means for the future of work, why entrepreneurial thinking is fast becoming a skill we all need, and what Alex is doing behind the scenes to make the UK a better place to build a business.
Whether you have ever thought about working for yourself or you simply want to understand what it takes to think and act more boldly with your money and your life, this one is for you.
Key Moments:
• Why 64% of Gen Z want to be their own boss and what that tells us about the future of work
• Growing up feeling like you never fit in and why your difference might be your greatest asset
• The emotional reality of building, scaling and selling businesses
• Why failure is more valuable than we give it credit for
• What AI is going to mean for all of us
• What Alex is working on behind the scenes as Entrepreneurship Advisor to the Chancellor
• What wealth really means to Alex, and her answer might surprise you
Chapters:
00:00 Intro
00:00:45 Fact or Fiction: Do 64% of Gen Z Want to Be Entrepreneurs?
00:02:05 Growing Up, Bullying & Never Feeling Like She Belonged
00:07:55 Why America Creates More Entrepreneurs Than the UK
00:12:16 The Moment She Stopped Playing Small
00:13:35 The Co-Founder Friendship That Changed Everything
00:15:43 Why We Need More Female Founders
00:18:27 Why Corporate Life Never Fit
00:20:53 From Safe Job to Starting a Business
00:22:03 The Idea That Became Hassle.com
00:23:03 The Phone Call That Changed Everything
00:25:08 How to Know When It's Time to Quit Your Job
00:26:42 What Great Employers Should Do Instead
00:29:35 Building an £8 Million Business Across Four Countries
00:31:23 Becoming a Mum While Scaling a Startup
00:33:31 Why Female Entrepreneurs Face Different Challenges
00:35:34 Starting a Business After Having Children
00:37:38 Why You Should Just Start
00:40:04 Selling a £32 Million Company
00:41:34 Success, Imposter Syndrome & Self-Worth
00:45:03 Becoming the Chancellor's First Entrepreneurship Adviser
00:50:49 Why Speaking Up Changed Everything
00:51:59 How to Stop Fear Holding You Back
00:57:18 The Future of AI, Work & Entrepreneurship
00:59:59 Happiness vs Contentment
01:00:21 Final Thoughts
Follow Alex Depledge:
Instagram: https://www.instagram.com/alexdepledge/?hl=en-gb
LinkedIn: https://uk.linkedin.com/in/alexandra-depledge-mbe-22b57a14
Website: https://www.alexdepledge.com
Follow Anna Brading:
Instagram: https://www.instagram.com/mentoramoney/?hl=en-gb
LinkedIn: https://www.linkedin.com/in/annajoybrading/
Website: https://www.mentoramoney.com
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